Compound and photoelectric device, image sensor, and electronic device including the same

Patent metadata

Field	Value
Publication number	US-12365697-B2
Application number	US-202117559069-A
Country	US
Kind code	B2
Filing date	Dec 22, 2021
Priority date	Dec 24, 2020
Publication date	Jul 22, 2025
Grant date	Jul 22, 2025

Abstract

A compound of Chemical Formula 1, and an organic photoelectric device, an image sensor, and an electronic device including the same are disclosed:In Chemical Formula 1, each substituent is the same as defined in the detailed description.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, or a condensed ring of two or more, wherein Ar 1 and Ar 2 are each independently present or linked with each other to provide a first condensed ring,
X is S, Se, Te, O, S(═O), S(═O) 2 , NR a , or SiR b R c , wherein R a , R b , and R c are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
R 1 to R 3 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a halogen, a cyano group (—CN), a cyano-containing group, or a combination thereof, wherein R 1 and R 2 are each independently present or linked with each other to provide a ring,
Y 1 is O, S, Se, Te, or C(R e ) (CN), wherein R e is hydrogen, a cyano group (—CN), or a C1 to C10 alkyl group, and
R 11 and R 12 are each independently hydrogen, deuterium, a C1 to C10 alkyl group, or a C6 to C10 aryl group,
wherein one of R 11 or R 12 is hydrogen or deuterium, and another one of R 11 or R 12 is a C1 to C10 alkyl group or a C6 to C10 aryl group,

wherein
Ar 2 and R 1 are each independently present, or
Ar 2 and R 1 are linked with each other to provide a second condensed ring and Ar 1 and Ar 2 are linked with each other to provide the first condensed ring.

2. The compound of claim 1 , wherein Chemical Formula 1 includes a cyclic group represented by Chemical Formula 2, and the cyclic group represented by Chemical Formula 2 is a cyclic group represented by Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 2-3:

wherein, in Chemical Formula 2,
Y 1 , R 11 , and R 12 are the same as Y 1 , R 11 , and R 12 , respectively, in Chemical Formula 1,

wherein, in Chemical Formula 2-1, Chemical Formula 2-2, and Chemical Formula 2-3,
R 11 and R 12 are the same as R 11 and R 12 , respectively, in Chemical Formula 1.

3. The compound of claim 1 , wherein in Chemical Formula 1, X is included in an X-containing 5-membered ring and R 1 and R 2 are linked to each other to provide an additional ring, and a portion of Chemical Formula 1 defined by the X-containing 5-membered ring and the additional ring is represented by Chemical Formula 3-1 or Chemical Formula 3-2:

wherein, in Chemical Formula 3-1 and Chemical Formula 3-2,
X is S, Se, Te, O, S(═O), S(═O) 2 , NR a , or SiR b R c , wherein R a , R b , and R c are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
R 1a and R 1b is hydrogen, a C1 to C10 alkyl group, a C6 to C10 aryl group, a C2 to C10 heteroaryl group, or a halogen, and a and b are each independently an integer of 1 to 4.

4. The compound of claim 1 , wherein in Chemical Formula 1, at least one of Ar 1 or Ar 2 comprises a heteroatom selected from nitrogen (N), sulfur(S), and selenium (Se) at a 1 st position of Chemical Formula 1.

5. The compound of claim 1 , wherein *—N(Ar 1 ) (Ar 2 ) of Chemical Formula 1 is represented by Chemical Formula 4-1:

wherein, in Chemical Formula 4-1,
Z 1 to Z 10 are each independently N or CR a , wherein R a is hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z 1 to Z 10 are CR a , R a 's are present independently or two adjacent ones of Z 1 to Z 10 are linked to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula 1.

6. The compound of claim 1 , wherein *—N(Ar 1 ) (Ar 2 ) of Chemical Formula 1 is represented by Chemical Formula 4-2:

wherein, in Chemical Formula 4-2,
X a and X b are each independently —O—, —S—, —Se—, —Te—, —NR a —, —SiR b R c —, or —GeR d R e —, wherein R a , R b , R c , R d , and R e are each independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group,
Z 1 to Z 6 are each independently N or CR x , wherein R x is hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z 1 to Z 6 are CR x , R x 's are present independently or two adjacent ones of Z 1 to Z 6 may be linked to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula 1.

7. The compound of claim 1 , wherein Ar 1 and Ar 2 of Chemical Formula 1 are linked to each other to form the first condensed ring, and *—N(Ar 1 ) (Ar 2 ) is represented by Chemical Formula 4-3:

wherein, in Chemical Formula 4-3,
Ar 1a and Ar 2a are each independently a substituted or unsubstituted 5-membered aromatic ring, a substituted or unsubstituted 6-membered aromatic ring, or a condensed ring of two or more, and
G is —(CR d R e ) n —, —O—, —S—, —Se—, —Te—, —N═, —NR f —, —SiR g R h —, —SiR gg R hh —, —GeR i R j —, —GeR ii R jj —, —(C(R m )═C(R n ))—, —(C(R mm )═C(R nn ))—, or a single bond, wherein R d , R e , R f , R g , R h , R i , R j , R m , and R n are each independently hydrogen, a halogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C10 aryl group, R gg and R hh are linked to each other to provide a first ring structure, R ii and R ij are linked to each other to provide a second ring structure, R mm and R nn are linked to each other to provide a third ring structure, and n of —(CR d R e ) n — is 1 or 2.

8. The compound of claim 7 , wherein Chemical Formula 4-3 is represented by Chemical Formula 4-3a, Chemical Formula 4-3b, or Chemical Formula 4-3c:

wherein, in Chemical Formula 4-3a,
G is the same as G in Chemical Formula 4-3,
Z 1 to Z 8 are each independently N or CR x , wherein R x is hydrogen, a C1 to C6 alkyl group, a C1 to C10 haloalkyl group, —SiH 3 , a C1 to C10 alkylsilyl group, —NH 2 , a C1 to C10 alkylamine group, a C6 to C12 aryl group, a C3 to C12 heteroaryl group, a halogen, a cyano group, or a combination thereof,
when Z 1 to Z 8 are CR x , R x 's are present independently or two adjacent ones of Z 1 to Z 8 are linked to each other to provide a 5-membered aromatic ring or a 6-membered aromatic ring, and
* is a linking point with Chemical Formula 1,

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Taejin
• Kim Hyeong-Ju
• Park Kyung Bae
• Shin Jisoo
• Yun Sung Young
• Lim Seon-Jeong
• Lim Youn Hee
• Hong Hye Rim

Classifications

• H10K30/80

  Constructional details · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title